While the Gilmore Girls fandom will likely never agree on who Rory Gilmore should have ended up with, the many narrative parallels between her and her mother provide clues about her perfect match. While the mother-daughter dynamic between Lorelai Gilmore (Lauren Graham) and Rory Gilmore (Alexis Bledel) has always been at the forefront of Gilmore Girls, their various romantic partners play a key role in both characters' development throughout the original TV series and its 2016 Netflix continuation Gilmore Girls: A Year in the Life. The latter famously—or perhaps infamously—ends with Rory announcing her own pregnancy, but her complicated love life only serves to further divide public opinion on who, if anyone, she should have ended up with.
Throughout Gilmore Girls seasons 1-7 and the Netflix reboot both Lorelai and Rory have serious relationships with just three people each. For Lorelai, there is her first love and baby daddy Christopher Hayden (David Sutcliffe), her season 1 fiance Max Medina (Scott Cohen), and of course, Stars Hollow diner owner and Lorelai's future husband Luke Danes (Scott Patterson). Rory finds her first love in the Clark Kent-esque Chicago transplant Dean Forester (Jared Padalecki), then moves on to Luke's leather jacket-wearing bad boy nephew Jess Mariano (Milo Ventimiglia), and finally college flame and fellow Yale student Logan Huntzberger (Matt Czuchry). There's also Paul (Jack Carpenter), but he doesn't really count as Rory completely forgetting about his existence is a running gag throughout A Year in the Life.
The various relationships of Gilmore Girls do more than simply give Lorelai and Rory memorable love interests to interact with, as they also help demonstrate just how similar the two characters really are. They come from drastically different upbringings, are both fiercely independent, and have their own separate interests, but creator Amy Sherman-Palladino frequently uses their love lives to illustrate growth in ways that are strikingly familiar. It is these same parallels that make it possible to determine that while Rory may end up raising Logan's child in the future, her real perfect Gilmore Girls match is and will always be Jess.
Rory & Dean Mirror Lorelai & Max Medina
Rory meets Stars Hallow newcomer Dean about halfway through the show's pilot, while Lorelai meets Rory its her love for Dean at the same time as Lorelai is finally able to open herself up to love, accepting Max's proposal. While the guys aren't very intellectually similar, they are both kind and caring individuals who come from humble familial origins. They represent a very specific time and stage in Rory and Lorelai's life that neither can return to (not for lack of trying on Rory's part). They were also both left heartbroken multiple times as the Gilmore girls worked out their individual issues on them in some not-so-nice ways. Max was left on the eve of his wedding to Lorelai, and is seen a year later still struggling to get over her. Dean was strung along for months after Jess returned to Stars Hollow, then later broke up his marriage by having an affair with her, only to be edged out once again by another guy.
Rory & Jess Mirror Lorelai & Luke Danes
The parallels between Jess and Luke are a bit more obvious, especially in Gilmore Girls season 4, episode 21 Luke is finally able to ask out Lorelai thanks to an assist from some self-help tapes, and this step inspires Jess to finally spill his emotions to Rory, claiming "I know you couldn't count on me before, but you can now. You know we're supposed to be together." A confused Rory rejects him, but both Luke and Jess take huge personal steps at the same time, and it ultimately makes them both better, more emotionally healthy people.
Rory & Logan Huntzberger Mirror Lorelai & Christopher
The final comparison is also the most obvious one. Rory meets college flame (and future baby daddy...probably) Logan Huntzberger during her sophomore year at Yale, and the quick-witted, charming scion is the spitting image of her father, Christopher. Both Gilmore Girls' original ending, they truly loved and ed one another. Had the timing been right it's likely they would have gotten married, as Rory really did want to say "yes" to his proposal in season 7—much like Lorelai really did want Christopher to be the guy for her before realizing it was always going to be Luke.
Gilmore Girls' Original Ending Makes These Parallels More Obvious
Long-time Gilmore Girls fans will know that Amy Sherman-Palladino had the show's last four words—"Mom? Yeah? I'm pregnant."—planned out well in advance, and finally got to deliver them in the Netflix reboot, Gilmore Girls: A Year in the Life. Amy and Daniel Palladino famously left the series before season 7 so it's impossible to know for sure how events would have played out had they stayed on. The end result would have been Rory having a baby right out of college, however, still in her early 20s instead of her 30s as was portrayed in the reboot. While the parallels are ultimately still there, they would have been much more direct in Gilmore Girls' original ending. The series was always about the cyclical nature of Lorelai and Rory's mother-daughter relationship despite their different upbringings and aspirations. As the show's beloved theme song says, "Where you lead, I will follow".
A flashback episode revealed that a young Lorelai and Christopher wanted to escape their parents by running away to Europe together, until Rory's unexpected conception put a hault to their plans. Lorelai ended up making it to Paris with Christopher, albeit many years later in Gilmore Girls season 7, but their impromptu marriage wasn't what she expected. Likewise, in Gilmore Girls: A Year in the Life it's revealed that Rory went on to find short-term success in journalism, with one of her pieces for the New Yorker gaining serious traction, but her dream of becoming the next Christiane Amanpour didn't play out the way she expected. While Rory never really talked about wanting kids, leading this revelation to understandably rub some fans the wrong way, her pregnancy was the last piece of Amy Sherman-Palladino's narrative puzzle. This ending also brought Lorelai full circle, presumably allowing her and Luke to become the parents she always wanted out of Emily (Kelly Bishop) and Richard Gilmore (Edward Herrmann) while raising her own kid.
Gilmore Girls' Parallels Make Jess Rory's Perfect Match (Not Logan)
Rory and Logan had plenty of opportunities to end up together, but never pulled the trigger. If it was going to happen, Logan certainly had the resources to make it happen logistically, and Rory was clearly open to long-distance relationships (sorry, Paul). Rory was understandably upset when Logan announced his engagement, putting an end to their affair, but she also didn't fight very hard for him or the relationship.
Gilmore Girls' cyclical narrative makes Jess Mariano the perfect match for Rory in a future beyond Netflix's reboot. The two got together far too early in life. Jess still needed to work through a mountain of emotional issues and Rory was too young to understand that fixing him shouldn't have been her responsibility. Still, the two needed that experience. Jess and Dean were a cute couple originally, but it became clear the older they got that they simply didn't have much in common beyond their feelings for each other. Milo Ventimiglia's Jess taught Rory what it was like to be in a relationship with someone who challenged her intellectually, and because of this their chemistry was undeniable. Meanwhile, losing Rory and dropping out of school inspired Jess to get his act together, maturing greatly and pursuing his ion for literature—something the two share.
Jess and Rory continuously challenge each other in ways that make them better. It was Jess returning to Stars Hollow in Gilmore Girls season 6, delivering some tough love, that forced Rory to rethink dropping out of Yale and cutting ties with her mother. Gilmore Girls: A Year in the Life shows Rory temporarily giving up on her goals, moving back in with her mother, and taking an unpaid job at the Gilmore Girls match.